Tommy Gun Love
by Kisshulover1
Summary: 1940's and the Yanks are fighting in WWII, swing is now the new music craze, and monsters are running rampant in cities like they always have. Nothings' new for Dean Winchester, lead Hunter in the Mobster Gang "Team Free Will", that is, until Dean gets a new assignment-something about guarding some guy running away from home and a whole mess of trouble. Mobster AU: Destiel/Sabriel
1. Job on Our Hands

**So this is my first Supernatural Fic set in the 1940's, chock full of monsters, blood and guys, romance, strife and all other sorts of goodies. This chapters song is "**Sing Sing Sing**" By **Benny Goodman**. So sit back and enjoy this Mobster Destiel Fic from me to you! I do not own Supernatural or it's characters, however I do own this fic!**

…

The shot of Old Fitzgerald Bourbon Whisky went down his throat like a flame, engulfing his mouth and tongue- hot and scalding with a bitter tinge to it towards the end. It did just the trick to shake the hunter up enough to gather his wits about him as he swallowed the amber colored liquid.

Well, whatever wits he had left in his already muddled up head.

The night hadn't gone well for the older Winchester. No, not in the slightest.

What should have been a routine kill for a haunt in an old textile factory, quickly grew into what Dean could only describe to be a frantic fight for his life. Who knew Ghosts could be such a pain in his ass?

The gig Bobby rung him up about this morning sounded nothing more than a spirit lingering around some run down old factory. Nothing too out of the ordinary, just a few hours of research at the library that he had his kid brother Sam do for him - seeing as how Dean really had no contentment to sit himself down in one of those dusty libraries and read till his eyes grew cross eyed.

It was a little after the clock in his house blared Twelve O'clock that he got the call back from Sammy that there was a suicide back in the twenties of one Elizabeth Goodritch. She had apparently stabbed herself with her sewing scissors in her throat - nice and bloody and gruesome. Just the way Dean liked it. Nothing a good ol' routine salt and burn tactic couldn't solve.

Oh damn was he ever wrong.

Turns out the Dame was never buried but cremated instead into a pound of ash - the nice and furious Ghosts usually are, Dean had come to realize early in life.

That being the case, Dean had decided to go all in, guns ablazin' to take care of this twisted broad before she slit some other poor helpless construction workers throat in the dead of night. Rushing into things usually worked for Dean, it meant he lacked emotion - and in a job like this, sentiment can get you buried six feet under. If you're lucky.

However, two sawed off shotguns, a whole dozen rock salt rounds under his coat, two silver knives in sheaths down the small of his back - and all of them lost except for a few capsules of rock salt - not enough to throw at a Demon to make the damn thing flinch.

To say the least, it had gone horribly wrong fast.

Elizabeth Goodrich must have been one uptight bitch in life, because she was a major psychopath in death. She came at Dean with nails raised, eyes sunken in and menacing looking - oh, and a big ol' pair of cloth cutting scissors in her hands too, you know, the ones she used to kill herself with all those years.

Anyway, what should have been an hour job turned out to be three and it left Dean pretty low on the fun meter, hence the drained hunters visit to one of the only hunter friendly bars in town, the _Road House_.

It was a nice place - not exactly the Ritz, but the live band was good on Fridays and Saturdays, the whisky flowed from the bottle easily, and there was always a nice Dame or two at the bar for Dean to get his eye fill. But not tonight. No, tonight he felt like getting piss drunk till he passed out. Screw conciseness, that's what he always said.

Taking another tentative sip of his bourbon he ran his tongue on his pearly whites and sucked the inside of his cheek. _Damn the whisky here is strong_, he thought with a pleasing smile. The better to uplift this rotten mood.

He had been waiting here for a little over twenty minutes, soaking up the smell of cigars and cigarettes, of giggles from pretty women with rosy cheeks and curly hair, and listening to the clatter of chips and the fanning of decks of cards on stiff tables. It was music to his ears. No screaming, no crying, no blood, no gunpowder blastin' and not a single supernatural son of a bitch in sight. Oh boy did he love the _Road House_.

However, he wasn't just lounging around here for kicks. No, Bobby had sent a telegram to the _Road House _while Dean was out dealing with Miss Bitchy-Undead. Bobby knew Dean like the back of his hand, figuring that after the oldest Winchester sent the ghost to rest, he'd be off to the bar to cool down.

The message that Dean received in chicken scratch sloping writing from Mr. Singer was straightforward enough, exactly like Bobby. "_Got that Job for ya' that I've been telling you about. Meet me at the Road House at Five and don't be late, Idjit_." The wryly older hunter sure did love to ruffle Deans feathers, not like he minded too much. Bobby was like a father to him ever since his own dad passed away, he could call Dean Idjit all he liked - Dean would never tire of it.

His fingers began to crease the little folded paper in two, nice lines forming along it's edge. The note was simple enough to jog Deans memory back from a week or two, about a certain conversation he had had with Bobby over a flask and two glasses of chilled ice.

It was a job, but not like anything Dean had ever handled or taken before in his long years as a hunter. It wasn't a raid, wasn't a hit and run, wasn't a rescue mission or a drugs bust on a house full of Demons - it was, well, to put it simply. Baby-sitting.

Now, Mr. Singer hadn't actually called it baby-sitting, instead he had very persistently described the job at hand as needing Dean to be a Body-Guard and Teacher to a new pupil. To which Dean snorted, called Bullshit, and became increasingly on edge about even accepting the task. It just felt too out of ordinary of his nicely straight forward career which entailed of shooting the bad guy, burning the body and receiving the doe at the end of the week to pay the pills. Simple, Easy, and fun as hell - just like Dean liked it. Baby-sitting some Bunny-Boy from the sticks however, did not sound fun, not one bit.

But apparently three weeks ago Bobby had got a telegraph from some kid in Louisiana wanting to join their little rouge gang of hunters headed by Mr. Singer. According to the older Hunter, the kid had potential. He was pretty young, healthy, strong, and had some God damn impressive reflexes that made him into a true warrior - a _weapon_ was the word Bobby used, which irked Dean to no end.

In the telegram that the kid sent Bobby he explained his situation clearly and precisely. He no longer wished to live under his Fathers roof with his brothers and sisters who were not the nicest people in the world. He wanted to live on his own a bit and 'see all the wonders of creation' or some other bullshit yuppy crap like that.

To Dean it just sounded like the guy had daddy issues or something - wanting to fly the nest and explore the town, city, the whole world. Sounded like a sap with a few screws loose to Dean.

But what really bothered Dean, what really got under his skin was the fact that the guy wanted to try his hand at becoming a hunter. And that just didn't sit right with Dean. Folks don't _want_ to be a hunter - they just become one. You see something horrible like a lady being dragged under a sewer grate screaming for help, have something horrible happen to you like losing your daughter to a shifter who couldn't stave off his appetite, or have your arm bitten off by a ghoul before someone shoots the fucker dead - and you just become one. You pick up the sawed off shot gun, shoot the mothers head off and move onto the next one. That was the life of a Hunter, that was the life of Dean Winchester, and he sure as hell didn't pick it.

Dean sighed through gritted teeth and ran his hand over his hair, ruffling it's shortness some but not by much, the grease in his cropped locks keeping it nice and slick.

He flicked his fingers over the tightly folded telegram again, running his sea-glass colored eyes over the pen ink that clotted slightly from Bobby's haste to write it.

Honestly, the job didn't sound so appealing to the young hunter. Dean's plate was already filled the brim and heaping with guts and severed body parts and everything else nasty and vile imaginable. He didn't think he had the time to teach a Green-Horn all the ropes. Demons had been getting into the drug business, and the number of Cross-Road workers had doubled. The Shifters were acting up along the west of the city and the pack has just been growing like a weed, not to mention all the un-dug bodies lately that were suspected to be the activity of ghouls. There just wasn't enough time.

It wasn't training the guy that was the problem - Dean knew how to mould a good fighter, a good shooter outta' anyone. He had helped his younger brother Sammy through this line of work, had seen him come out scratched and battered, but alive just the same, and stronger than ever. He'd helped Chuck get through his anxiety and taught him how to knife a beastie in the throat. He had showed Jo how to draw devils traps on ceilings where the demons were less likely to look. Dean knew how to take care of people better than he knew how to take care of himself. He was good at teaching when the people wanted to learn - but that didn't mean he wanted to take on some fresh doe-eyed pup who thought the job was glamorous.

Being wrist deep in decaying bodies and slathered in flaking blood and other sticky stuff was not glamorous.

However, Bobby said the guy's father was willing to dish out the cash to pay for his sons availability to go into training and to work for "_Team Free Will_" as their group of Hunters became known as in the area.

Now Dean was no money grubber, but cash for weapons in this day and age while the good ol' yanks were fighting the Germans was scarce and hard to come by without the Chopper Squad confiscating the dough or asking questions. Connections were thin and hard to come by already. Their little group of hunters needed more money to buy salt rounds, machine guns, books on information, and just to be clear - silver bullets did not come cheap.

Plus another benefiting factor of taking the new guy in was that Dean could use the money from his added paycheck to buy some parts to fix up his baby - a 1940 Black Cadillac Imperial. His damn near pride and joy.

Deans smile suddenly turned grim as he huffed in gruff aggravation.

Well. It seemed that Dean Winchester was a slave to money, besides the fact that he didn't think he had it in him to tell Bobby no.

After raking his short nails over his still dusty and sweaty face Dean slammed the empty shot glass down onto the bar counter, the glasses rim coming back sticky and salty from the bars unclean surface. Dean winced and decided he should probably switch from whisky to beer for the night, lest he wanted to get picked up by the Chopper Squad for milling the streets all drunk and disorderly. And as much as slurring his words and blacking out in the middle of the street actually sounded appealing - he had to go to work tomorrow bright and early to train the new Rich-Kid. Plus, Bobby didn't seem like the kind of Boss who would be all too thrilled to have one of his hunters smell like Bourbon and throw-up. No, Dean wouldn't want a repeat of that again.

So, being the classy gentlemen that he was, he, slammed his hand on the bar table, trying to act more cheery than he felt and called out to the Bartender, Ellen whose ability to sell Dean liquor at this moment made her his new best friend.

"Hey Ellen." Dean grins slow and lazy, his eyes shining and watery as he gestures to the tiny little shot glass on the bar table, still wet with whisky clinging along it's edges. Nice and amber looking in the smoky light of the bar.

The woman, age showing slightly on her face underneath the pastel powder of her cheeks, looks to the young hunter on his stool, her eyes narrowing slightly, hand making its home on her hip.

"What can I do for ya' Dean?" Her voice is a bit throaty and tired from answering previous hunters questions and giving out information all day but her voice makes Dean smile, as Ellen reminds him of his own Momma' who died way back when he was just a little brat. Two parents down and buried six feet under, sounded more and more like a Hunters life than Dean cared for at times.

"Can I trade in my glass - I wanna' get some beer in my gut while the night's still young." Dean gave her that shit-eating grin that he was all too fond of keeping on his lips while he gestured to the outside, the spring weather casting it's last warm tendrils of light into the sunset as the outside oil lamps were lit to give the street some more light.

Ellen looked to Dean with her own little huffing smirk, her fingers still as she paused from wiping a wine glass clean till it shown bright and clear.

"Sorry big boy, one more drop of liquor for you and I think you'll be pushing up daisies on the side of the road." Her eyes smiled as she placed the wine glass underside up on the shelf, the tinkering sounding like little glass bells amidst the somewhat loud clamor of the other patrons who were slugging down their own drinks.

Somewhere off to the side where the bar's record player sat prettily on a little cheery oak table, Jo, Ellens daughter, was fiddling with the needle on the contraption, trying to find the right song for the evening to lighten the mood. Every Hunter needed some soothing tunes to block our the hideous things they've seen earlier in the day.

"Awww, you're no fun." Dean pouted like a regular charmer.

"Never said I was." Ellen never wavered, catching on to the act quicker than wildfire.

All of the sudden a great blaring was heard from the crackly old record player to the side, the music coming out sweet and twang-y through the air. Benny Goodman's "_Sing Sing Sing_" trumpeted outward, sounding oh-so good to the ears, getting the body jumping and swaying - too bad Dean's blood was sluggish in his veins at the moment and his bow-legs too damn tired to even pick themselves up from the bar stool to shake 'em out.

However that wasn't the only sound that he Winchesters ears picked up at that moment.

A few bars into the song where the drums began to beat furiously and the patrons began to waggle their fingers and holler, the Road House's wooden door made a creaking sound, the bells above the opening crinkling to notify that another customer had made their way into the hustle and bustle.

It was then that Dean's ears pick up the gruff voice of Bobby above the grainy music. His voice was nice and assured, somewhat giddy even. If giddy could ever be a word used to describe Bobby Singer.

"You'll like 'em. He's not too gifted in the smarts department but he ain't no goon. He'll take care a' ya'." Dean heard his boss speak behind from where Dean was sitting. The Winchester only needed a few seconds to understand that Bobby was more than likely talking about him. Deans eyes squinted in quiet agitation at the insult that was directed towards him, knowing Bobby was only kidding about Deans intelligence…At least he hoped so. So then who was the other person Bobby was talking to?

"That is good to hear. I am sure I am in capable hands." Came the reply in a voice so damn smoky and gravelly Dean suspected it had to of come from a smoker. The voice sounded like smooth velvet that had been charred by flame and gasoline, then stepped and smudged into the gravel fifty times. It was an interesting voice to say the least and it left Deans arms all tingly and fidgeting.

Taking the opportune moment to turn himself from his bar stool to face his boss and his new companion with a wink and a wise crack about the old man and his own intelligence, Dean turned to see a sight he really did not know what to think of.

What was once a prepared glare for Bobby turned into a wide open mouth in the shape of an 'o', and eyes even wider to match. For, standing right before the bow legged green eyed hunter, was a stranger more beautiful than any dame or doll yet more rough around the edges than any sober man.

Tucked in nicely into a suit that screamed tailored, was a slender man a little bit older than Dean. Gruff chin in need of a shave and thin shaped lips made up the mans face as well as amazingly blue eyes that nearly shocked Dean off his seat. This man was gorgeous….

Dean was suddenly and a bit annoyingly brought back down to earth from his insistent staring of the blue eyed pale man before him by Bobby.

Clearing his throat, the universal signal for, _Pick your Jaw up from the floor boy, we got work to do_, Bobby sent a silent signal for Dean to listen and listen good lest he wanted graveyard duty tomorrow night.

"Hey Bobby… Whose you're friend?" Dean swallowed softly, his throat feeling like he swallowed a fist full of sand. Dear God those eyes, cornflower blue and crystal clear, as if Dean could just swim in those beauties…

Bobby could only roll his eyes at the younger hunter before he jutted a thumb at the tall, taller than Dean, man standing patiently next to him.

"Dean Winchester, meet Castiel Novak, You're new assignment and partner."

…

**Hey Guys, so this is my first Supernatural AU Fic and I want to make sure I'm doing it right. Also I'm trying hard to make everything accurate, however this fic is historically accurate to the last detail! So, tell me what you guys think? Is it worthy of the Supernatural Fandom? **


	2. Angel of the Lord

**Hey Guys! I got some great feedback so far for this fic and I am so damn excited to update the next chapter! I really hope you enjoy it, especially you, **yetanotherwallflower**! **I do not **own Supernatural but **I do own **this fic! This songs chapter is **Mr. Pinstripe Suit **by **Big Bad Voodoo Daddy**. Enjoy, lovely readers!**

…

Dean could only stare with blinking green eyes at the man named Castiel who looked to be just a bit older than him. His age certainly showed in his cornflower blue eyes. There was a bit of wear, a bit of a shadow underneath his eyes. His gaze showed him to be a bit wiser, like he had seen a hell of a lot of trouble and dispair- things that would give Dean nightmares just to have a few glimpse of.

Dean licked his now parched lips, staring into those eyes that screamed of times long past.

Oh, this man was definitely hunter material.

However, his clothing sure as hell wasn't.

The only thing that stuck out like a sore thumb on the guy was the outfit he was wearing, which just exuded a "_Rich Boy_" attitude. He looked to be right out of some hot-shot movie star film - not some rough and tumble hunter with battle scars all over and a body stinking of alcohol. In fact the poor sap looked like he'd never thrown back a bottle of beer in his life. Well, a sober hunter would just not do for the job.

The more Dean looked at him, however, the less he really cared about how flashy the mans clothes were. In fact, just staring at the guy he could say they somewhat complimented him - hunter friendly or not. Because damn would Dean be lying to himself if he didn't think they made Castiel more attractive than any kitten at the bar.

With that nicely pressed pinstripe suit of smoky grey and the hinting of a new tight black vest underneath, he looked as if it was the first time the man was wearing it - Dean would place money on it to be true.

Then their was his shoes. New and shiny with leather oil, black and white wingtips that practically shone in the wavering light of the bar. Dean would bet a nice crisp twenty that he could see his face in them, could count every goddamn freckle on his cheeks.

All that and a sharp blue tie to match is eyes and a big heavy trench coat over his skinny arm that he was nervously plucking at with his index finger and thumb, like some dumb security blanket. Oh Dean knew he had hunter potential in him somewhere, he just did not look the part. At All.

But what really puzzled Dean to no end, was the way he was looking at this man that he had never seen before in all his thirty-years on this earth. Now, Dean knew he was not like other men - he knew that for a fact, and it was that little bit of knowledge in the back of his mind that explained to him in glaring bright red color across his brain, why oh why he was staring so intently.

Dean was different. Not totally, completely unusual, but different just the same. He shot things in the dark with a machine gun, he dug up graves and salted and burned the remains of bare boned corpses, he had a small arsenal in the back of his Cadillac that held more voodoo-hoodoo objects than any self respecting hunter should. But that wasn't the thing that alienated him, that made him so totally atypical that it could put his very life on the line by even saying it to certain folk around these parts.

He liked women. He liked them curvy, curly, and everything in between. Black haired, Brunette, Blond, Red-Head, it didn't matter to him. He had a thing for their eyes, the brighter the color the better. He had a thing for their lips, supple and soft were the best. He had a thing for their stomachs, nice and soft - kissable. He liked women.

Dean however, also liked men.

Tall ones were the best, skinny and tall. He had no preference with hair color or eyes, just as long as the mans gaze was bright. He liked them the most, men. Girls were lovely and set his heart ablaze, but looking at a man did more to him, gave him more. Instead of sending his heart aflutter it made it sputter out of control. He liked men the best.

And saying that to a room full of people in this day and age would surely get him strung up so high by a rope, he'd be swaying in the wind for days.

So Dean made sure to shut his mouth around town and to only tell a few people. Sam, Ellen and Jo were his confiding force of comfort. They swore to support Dean and not treat him like he was sick in the head and send him to a mental hospital. They listened to his rants and made sure to not ask questions when he went out late at night and came back late in the morning for work. That was it. No one else knew his struggles, and no one else should. Dean was too much of a chicken shit to tell any one else for fear of his life to end at the hand of some bigot swinging a noose.

Of course, only telling a few people meant his pickings were slim. Sure he'd go take trips to the small district down town for a romp, but then he'd hate himself after for being such a coward and usually ended up drinking himself into a damn stupor. It was not fun and he was not proud, but it had to be that way - at least that's what he had convinced himself.

But looking back at Castiel, at the mans thin pink chapped lips that Dean bet tasted better than any of Ellen's Rhubarb pie, Dean began to feel that tightness at his gut and that tug at his heart, that voice in his head reminding him that he didn't always have to hide, he didn't always have to scare himself silly with nightmares and harsh words and what ifs. He could indulge in small ways, in secretive ways until he was ready to embrace and be embraced. And boy could he see himself doing some pretty nice and intimate things with Castiel.

"Ya' just gonna' stand there all day lookin' like a dumbass, or are ya' gonna' show Castiel to the back room? Huh, boy?" Bobby's harsh voice startled Dean right from his stupor, his face flushing a horrible red, making the room seem hotter than it should have been.

"Huh? Uh, yeah. Come on, Cas." Dean spoke hurriedly, trying to not act like the biggest buffoon this side of the country.

Ellen however, seemed to catch on real quick to the Winchesters flustered face and gave him a snort of laughter and a knowing smile which Dean waved off with a quick sour frown.

He could let himself indulge in day dreams yes, but he knew for a fact that hinting to Bobby that he occasionally swung for the other team would complicate things. Bobby was a father figure to him, and he wouldn't let anything jeopardize their relationship. He could keep is secrets, it wouldn't hurt the old man.

So, sliding himself off the red leather bar stool he scrunched his fedora between his fingers and stood on his own two shaky legs to led the way.

But before he could get too far, there was that voice again, the one that set Deans bones to jumping.

"Cas…?"

Dean cleared his throat in nervousness, hoping silently that he didn't offend the guy.

"Yeah. Cas. It's a nickname - what, they don't have nicknames down in Louisiana?" Dean teased the man, looking back to see Cas' face scrunched up in confusion, his head tilted to make him look like a lost puppy.

Oh this man would be the end of him.

"No, we have nicknames in…Louisiana. It is just that I have never had the honor to uphold one." Cas reasoned, his voice still hinting with confusion and what appeared to be new found awe at even having a nickname bestowed upon him.

_Damn, if he isn't the weirdest little Sheik in these parts…. _Dean thought to himself with a hidden smile.

"Well, it's not that big of a deal, but since ya' don't mind it, Cas it is." Dean huffed with easy laugher as he began to walk by the _Road House's _tables, passing Jo along the way who was done with the record player and instead was wiping down some tables that her Mamma' said needed cleaning.

The pretty blond who was like a sister to Dean looked up from her work with a smile that shined brighter than the moon on a harvest night.

"New meat?" She asked playfully to Dean and Bobby, wiping her brow which was gleaming softly with sweat. She made a show of a grin at Cas who looked all but terrified out of his mind at the prospect of being '_new meat_'.

Dean caught on real quick to the mans widening eyes and placed a hand on Cas' shoulder to calm the man down, his fingers tingling as they felt the expensive material of the dark haired mans suit.

"Relax man, Jo won't hurt ya'. She's no man hunter." Dean said, resulting in those shockingly icy eyes to smooth and relax a bit.

Jo flashed teeth at that, her smile widening.

"Oh yeah, I'm safe - but Dean here? Watch out for him. He's a real _Lounge Lizard_." Jo winked to Cas, the black haired man's face contorting into confusion yet again.

"What do you mean he's a Lounge Li-" Cas was about to inquire when Dean cleared his throat rather loudly, his voice rising above the crackling music, making a few of the hunters enjoying their meal or whiskey to take notice rather quickly.

"Nothing Cas, she's just messing with you. Come on, let's get you settled in with some equipment." Dean hustled Cas along inside a door painted roughly in brick red, the door knob glinting nice and pretty against the glass lamp light.

After Cas was pushed through, Dean sent the nastiest glare he could towards Jo, the blond only shrugging and going back to her work, the inklings of a smirk on her face evident. If Dean wasn't so sure she'd tear him a new one, he'd yell her ear off. The damn girl was all forked tongue and teeth. A good hunter but damn did she know how to push Dean's buttons. He'd have to never leave her alone with Cas if he wanted to keep his new blooming secret to himself.

Once inside the rather uninhabited dark room, that served as the 'interrogation' room for new recruits or to persuade information out of none-too friendly guests, Dean made his way to a set of chairs, plopping himself down in one like a cat ready for a nap.

Without a word Cas set himself down, nice and polite in the chair across from Dean, that stupid trench coat snuggled nice and warm on his lap like it always needed to be near him. Dean would have to ask the guy later about it.

It was a few seconds later that Bobby came in last, shutting the door nice and tight with his foot for privacy, his hands preoccupied with a folder and a mug of cold beer that he swiped from the bar. He sat down next to Cas with a sigh and handed the rather thin folder to the Winchester before nursing his beer to his lips.

Dean's fingers closed around the manila envelope, a string holding the thing tightly closed. Using his nails to work the knot he finally plucked the thing open to reveal a few newspaper clippings of what looked like a big old southern house with a wrap around porch and a rocking chair out front. Sitting on the porch was what looked like a chubby baby Cas, his arms trying with no avail to wrap around the waist of a man who looked to be Castiel's father.

"That is a family photo, my father, Jimmy Novak, and I at our house when I was no more than two years old." Cas spoke softly, evenly, as if his voice could barely do the picture justice. As if he longed and wished to be that kid in the photograph again just one more time.

Dean knew instantly how the other man felt. He wished he could go back to when his mother was still alive, when his Dad was still there for him and Sammy and not touring the world for Supernatural chaos. But now Sammy and him were alone and there was no hop in wishing for things that wouldn't come true. It was just nonsense.

Under the graying photo was a few newspaper clippings, some stuff about Cas and his achievements in high school and College - Well, a college man, Dean had himself a thinker on his hands!- and a resume with a list of qualifications.

Everything looked amazing, as if Cas was graced by God or something along that line. Not a blemish on his record - he could see now why Bobby had wanted him to join Team Free Will so badly. Sure, Cas was a rookie - but a Rookie with Cash and familiarity with Supernatural creatures? Jack pot.

"Well, I'm impressed." Dean sent a friendly grin to Cas, the other man returning it with a shy smile that felt a little new on his face. Dean figured the guy just didn't have reason to smile a lot.

"So, you're running away from your family? That's what it says in this telegram." Dean sat back down nice and easy in his chair, a _I'm not judging _you look plastered nice and soft on his face. He wanted Cas to relax, trust him enough to tell him his problems and troubles. Dean would listen. He was used to hearing all of Sammy's whiny bitch fits anyway.

Castiel seemed hesitant at first, but after a reassuring look from Bobby, to which Dean noticed calmed the man a lot, the nicely dressed man began to speak.

"I'm not exactly, running away from home, as you put it. I am merely taking a vacation, what I hope will be a long one." Tension seemed to roll off his words into the cool air of the room, the only source of light as small stained glass lamp on a chain above them.

"Trouble with your siblings?" Dean inquired, wrapping his hands together to sit them nicely on the table in front of him.

Cas visibly fidgeted at that last question, wringing his fingers tighter into the trench coat under the table. Dean almost wished he hadn't brought up the mans family - perhaps it was a touchy subject.

"Trouble is an understatement. I have five siblings and two uncles living with me, with a father who is absent most of the time." Cas sighed, his eyes glassy, misting with emotion that seemed to be hard for the man before Dean to convey.

"They…They fight immensely. It's gotten to the point where I cannot go home for fear of their everlasting bickering. My eldest brother and my two uncles, they are the worst. They are bullies at best, always controlling what me and my other brothers and sisters do." Castiel murmured quietly, not wanting to reveal all about what Dean guessed was a truly pitiful family relationship.

At least Dean never had it that bad, to the fact where he couldn't even stand going home.

"That's rough man, real rough. I'm sorry." Dean did his best to try and convey to the man that he really did feel bad for him.

Castiel looked upward to meet the other man with a small smile of thanks that reached his eyes.

"I'm just glad to be away from them for now."

Dean nodded and smiled, trying his best to find a topic to lighten the depressing mood that was growing thick in the air.

"So, you're from Louisiana?" Dean asked with a lazy grin, one that made Bobby roll his eyes and take another sip from his bear, his beard coming back speckled with amber dew that made him look just plain ridiculous.

"Oh. Um, yes. I was born and raised there all my life." Cas lied right through his teeth, knowing damn well that it was a sin, but not seeing much choice in the matter. Bobby told him it was okay to lie in this situation, it was a white lie, nothing more. Castiel barely believed him.

Dean nodded his head, his smile never wavering.

"That so? Ever been to New Orleans?" Dean asked nice and gentlemanly, his eyes careful to look for discomfort in Castiel's eyes.

"New Orleans? Why, I - I live there! Yes, right in good old new Orleans!" He spoke rapidly, quickly, the lie eating right through his lips, making them burn. This was a horrible idea, a vile, disturbed idea. And it was all his.

"Oh? Well, ain't that just a coincidence? My Daddy worked a job there awhile ago - took Sammy, my brother, and I." Dean kept his voice nice and controlled as he red Castiel, looking to see the sweat flush against the mans neck, watching as the blue eyed man bobbed his leg up and down as if it was a nervous habit. Dean knew right then and there that he was lying, and horribly at that.

"Is that so? Well, New Orleans is lovely for a visit." Castiel panicked, feeling like he was digging himself into the deepest pit imaginable, so deep that it wouldn't even contain his older brother Lucifer. _Just smile, keep smiling. _

"Mhmm… It's a right damn hospitable place." Dean agrees, his eyes flickering to Bobby. The old man just kept his eyes on the rim of his almost finished beer, his teeth looking clenched in his jaw, as if he wanted to say something but thought better of it.

It was as big a tip as any to tell Dean that something was way off.

Pushing himself up from his chair, Dean walked over to the lonely metal cabinets that ran along the wall in cold colors of grey, silver, and black. It was the only decoration in the room save for the lamp, chairs and table and it made everything seem a little bit more gloomy. A little bit more like a torture chamber.

Creaking one of the drawers open Dean pulled out a bundle wrapped in soft light blue cloth, cradling it against his fingers like it was a new born baby.

From behind him Dean heard Bobby fidget in his seat, the sound of the beer mug being raised and lowered onto the table with a bit of a shake. The Winchester slowly turned around to the sound, his fingers dutifully working to uncover the clothed object that was flat against his palm. A soft tickling was heard from inside the cloth, the sound of metal hitting metal. Castiel's stomach dropped immediately.

After sitting himself down nice and comfy in his seat, Dean placed the small bundle against the plain oak wood of the table, his lips whistling a short snappy tune before his eyes shot back up to Cas, a smirk on his lips.

"Ever handled a gun before in New Orleans, Cas?" Dean asked, unwrapping the last of the soft cloth before it slipped over the wood and metal of a Colt Detective Special with a three inch barrel, the cold surface of the gun glinting in the dim light. Cas's eyes flicked to the gun for a mere second of shock before he composed himself. Lying was a sin, something he cold barely swallow. But being in the presence of a gun? He wasn't bothered in the slightest. It's not like it could kill him if Dean chose to used it - to which Castiel prayed that the hunter wouldn't. It would surely put a damper on their already straining relationship.

"I…I have. Though I'll need a lot more practice with one than I'm used to." He managed to breath out, his eyes scanning the little weapon in front of him. In all honesty, Castiel has never touched a gun in his life. He's never had too. Resorting to such pitiful weapons had never once crossed his mind. This plan of his was definitely going to give him a big change in scenery.

"Well, we'll have to get you trained and used to it." Dean muttered to himself, flashing teeth in a grin that was meant to comfort Cas but only made him grow even more weary, his thumb swiping along his trench coat that was being bunched up on his knee.

"Well start him off on a Colt - nothing' with too big of a kick. He won't be ready for shotguns for a while." Bobby's gruff voice finally filled the silence in the room, save for Deans short nailed fingers running against the bumps of the gun.

_It's like he's caressing a religious object. _Castiel observes in wonder.

"Sure. We'll start small. Though it must be hard living in New Orleans and not being able to shoot a shotgun too well, what with all those shifters running round." Dean snapped the revolver against his wrist, making Cas bite his chapped lip, feeling another lie burst through his mouth.

"Ah. Yes. Very hard indeed. You cannot walk down the side of the street without smelling the scent of their fur or hearing their calls during the full moon." Cas spoke with wavering voice, his eyes flashing to Bobby silently for help but Dean only leaned forward, demanding Cas's glance on him as the hunter it back a fake frown.

"Oh really? That's funny, because there hasn't been a shifter pack in New Orleans since the early thirties - I should know, my Daddy took care of them all. So why don't you quit the bluenose act and tell me where you're really from?" Dean's eyes swerve from happy-buddy-buddy to serious in a split second, his hands stilling on the gun in his hand, the barrel pointed towards Cas threatening. Cas didn't even blink, silently congratulating the Winchester in front of him for solving the riddle. At least he didn't have to lie anymore.

"_Balls!_" Bobby cursed loudly under his breath, before he slammed the glass mug of beer on the table and leaned back, rubbing his eyes with his knuckles.

"You told me you were a good liar, boy!" Bobby spoke, to which Dean guessed he was gesturing towards Castiel who was running his hands soothingly over the tan overcoat, petting it almost.

"I never said such a thing. I said I would try my best at lying, and I did. Apparently my best was not good enough."

Dean huffed, his eyes never straying from Cas for even one second. He didn't want to let the man outta' his sight.

"Bobby, I swear, you better tell me what the hell is going on here!" Dean snapped fiercely to the older man, jerking his gun quickly for emphasis at Cas.

"Please, the gun waving isn't necessary. If you shoot me, I'll just heal myself." Cas sighed at Dean, as if he was wearily talking to a little child who was misbehaving, causing Dean's eyes to widen in anger. Attractive man or not, no stranger insults Dean Winchester without hearing his two cents about it!

"What are you? A Draft-Dodger? A Monster? Does Bobby owe you a favor?" Dean's voice raised above a shout, his nostrils flaring as he placed his left palm flat against the table, the gun never unsteadying from it's place near Castiel's face.

Bobby sighed in annoyance from his seated spot, looking to Dean like he was the biggest goon in the room.

"Boy, put that down before you do somethin' even more stupid." Bobby made a move for the gun but Dean pulled back, his eyes shining something fierce as he shouted once more.

"I will not! Tell me who this Wise Guy is!"

And then Dean's attention was brought back down from his screaming and hissing and spiting by the bluest color of eyes he had ever seen in his short existence.

With the most sincere expression possible, with that pretty little mouth, Castiel spoke slow and steady so as not to aggravate Dean more, realizing just how hot tempered the hunter was.

"My name is Castiel, and I am an Angel of the Lord."

…**.**

**Okay, so the ending is a bit meh. I blame sleep deprivation. Also, I'm sure you can tell that there are a lot of 1940's slang! Nothing a good old Google search won't elaborate - but If you would like, after every chapter I could define them under the authors notes - would that be advised? PLEASE REVIEW, I REALLY DO LIVE OFF OF THEM!**


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